INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, X5000HUA Córdoba, Argentina.
J Org Chem. 2012 Jan 6;77(1):460-72. doi: 10.1021/jo202012n. Epub 2011 Dec 19.
A two-step synthesis of six-, seven-, eight-, and nine-member benzo-fused heterocycles in good to excellent yields is reported. The synthetic strategy involves the generation of a new intramolecular α-aryl ketone bond by the photostimulated S(RN)1 reaction of ketone enolate anions linked to a pendant haloarene as the key step. On the other hand, an intramolecular C(Ar)-C(Ar) coupling led to the formation of five- and six-member benzo-fused heterocycles (9H-carbazole and phenanthridine) when an aromatic amide anion is competitively formed.
本文报道了一种两步法合成六、七、八和九元苯并稠合杂环的方法，产率良好至优秀。该合成策略包括通过酮烯醇化物阴离子与连接到侧芳基卤化物的新的分子内α-芳基酮键的光刺激 S（RN）1 反应作为关键步骤。另一方面，当竞争形成芳族酰胺阴离子时，分子内 C（Ar）-C（Ar）偶联导致五元及六元苯并稠合杂环（9H-咔唑和菲啶）的形成。
